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Octadecylamine, also known as N-stearylamine or 1-aminooctadecane, belongs to the class of organic compounds known as monoalkylamines.
These are organic compounds containing an primary aliphatic amine group.
Octadecylamine is a very strong basic compound (based on its pKa).
CAS: 124-30-1
MF: C18H39N
MW: 269.51
EINECS: 204-695-3
Synonyms
1-Octadecanamine;FENTAMINE A18;FENTAMINE A-86;OctadecylaMine, tech., 90% 500GR;1-Aminooctadecane Octadecylamine;OCLadecanaMine;CHaMine 9098;EighteenaMine
An 18-carbon primary aliphatic amine.
Octadecylamine is a kind of aliphatic amines compound being subject to industrial mass production.
At room temperature, Octadecylamine is as white crystals with the molecular weight being 269.5, melting point being 52.8612, boiling point being 232.12 (4.27 kPa), the flash point being 149 ℃, the relative density being 0.8618 and the refractive index being 1.4522.
Octadecylamine is slightly soluble in acetone, kerosene and methanol, easily soluble in carbon tetrachloride, chloroform, ethanol, isopropanol and toluene, soluble in alcohol, ether, benzene but insoluble in water.
Octadecylamine has alkaline property and can react with hydrochloric acid to generate adduct product.
Octadecylamine's toxicity is lower than low-grade amine.
Rat being subject to oral administration of 500 × 10-6 Octadecanamine for two consecutive years get no significant adverse consequences.
Octadecylamine has irritation effect on human skin and mucous membrane.
Octadecylamine can be used as the intermediates for organic synthesis such as for the production of octadecyl quaternary ammonium salts and various kinds of additives such as cationic thickening agent, mineral flotation agents, emulsifier of synthetic resins, pesticides and asphalt, antistatic agents, wetting agents, waterproofing agents, surfactants as well as biocides of fabric, color former of color photo and the corrosion inhibitor of the oil refining device.
Octadecylamine can be generated by the reaction of stearic acid and ammonia for generating octadecanitrile and further catalytic hydrogenation under pressure for further reduction of enamine.
Octadecylamine is a chemical compound that can be used as a raw material for the synthesis of colloidal gold.
Octadecylamine has been shown to have significant cytotoxicity and hypoglycemic effects, and is also used in the preparation of liposomes.
Octadecylamine is a component of polymer compositions that are used in the treatment of bowel disease.
Octadecylamine has been shown to increase water vapor permeability and has an electrochemical impedance spectroscopy profile with a rate constant of 0.4 s−1.
Octadecylamine also shows significant antimicrobial activity against Gram-positive bacteria such as Staphylococcus aureus, Streptococcus pyogenes, and Clostridium difficile, but not against Gram-negative bacteria such as Escherichia coli or Pseudomonas aeruginosa.
A white solid.
Insoluble in water and less dense than water.
Hence floats on water.
Contact may irritate skin, eyes and mucous membranes.
May be toxic by ingestion. Used to make other chemicals.
Octadecylamine, with the CAS number 124-30-1, is a long-chain primary amine characterized by its hydrophobic alkyl chain and an amine functional group.
Octadecylamine typically appears as a colorless to pale yellow liquid or solid, depending on temperature, and has a distinctive amine odor.
Octadecylamine is soluble in organic solvents such as ethanol and chloroform but exhibits limited solubility in water due to its long hydrophobic tail.
Octadecylamine is known for its surfactant properties, making it useful in various applications, including as a corrosion inhibitor, emulsifier, and in the formulation of coatings and adhesives.
Additionally, Octadecylamine can participate in chemical reactions such as alkylation and can form salts with acids.
Octadecylamine's long carbon chain contributes to its ability to interact with lipid membranes, which is significant in biological and industrial contexts.
Safety considerations include handling Octadecylamine with care, as it can be irritating to the skin and eyes, and appropriate personal protective equipment should be used during handling.
Octadecylamine Chemical Properties
Melting point: 50-52 °C(lit.)
Boiling point: 232 °C32 mm Hg(lit.)
density: 0.862
vapor pressure: 10 mm Hg ( 72 °C)
refractive index: 1.4522
Fp: 300 °F
storage temp.: Store below +30°C.
form: Prills
pka: 10.6(at 25℃)
color: White
Water Solubility: practically insoluble
FreezingPoint: 53.1℃
BRN: 636111
Cosmetics Ingredients Functions: ANTISTATIC
InChI: 1S/C18H39N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h2-19H2,1H3
InChIKey: REYJJPSVUYRZGE-UHFFFAOYSA-N
LogP: 4.33 at 25℃
CAS DataBase Reference: 124-30-1(CAS DataBase Reference)
NIST Chemistry Reference: Octadecylamine (124-30-1)
EPA Substance Registry System: Octadecylamine (124-30-1)
Octadecylamine appears as white waxy crystalline solid with alkalinity.
Octadecylamine is soluble in chloroform, soluble in alcohol, ether and benzene, slightly soluble in acetone and insoluble in water.
Uses
Octadecylamine can be used as the intermediates of organic synthesis for the production of octadecyl quaternary ammonium salts and many kinds of additives such as cationic grease thickener, mineral flotation agents, pesticides and asphalt emulsifier, fabric antistatic agents, softeners, wetting agents and waterproofing agents, surfactants, biocides, color former of color photo and the corrosion inhibitor of the oil refining device.
Putting the Octadecanamine in mixture with ethylene oxide in a molar ratio of 1: 2 for reaction at 150-190 ℃ can gives stearyl diethanolamine [10213-78-2] with a yield of 80%.
Stearyl diethanolamine belongs to a non-ionic antistatic agent and can be applied to polypropylene, polystyrene and ABS resin.
Octadecylamine is used in biological studies for the formation of ion pairing as alternative to improve encapsulation and stability and to reduce skin irritation of retinoic acid loaded in solid lipid nanoparticles.
Octadecylamine is used to surface functionalize different carbon nanomaterials (graphene oxide, carbon nanotubes) for different applications which include thin film nanocomposite (TFN) nanofilteration and carbon fiber microelectrodes.
Octadecylamine can be used for the preparation of butyrylcholinesterase/stearylamine films (Langmuir-Blodgett films) for use in enzymatic field effect transistor (ENFET) based biosensors.
Octadecylamine also forms films which can be used in ion exachnge systems.
Octadecylamine may also be used in the preparation of metal oxide nano crystals with controlled size and shape.
Octadecylamine is used:
To induce hydrophobicity in nanodiamond (ND) powders.
In the surface modification of graphite and fullerenes.
As a dual source of carbon and nitrogen in the synthesis of N-doped carbon nanotubes (CNTs).
To synthesize a single-chain cationic surfactant, bis(amidoethylcarbamoylethyl) octadecylamine.
Production method
Octadecylamine can be obtained from stearic acid via ammoniation and hydrogenation.
Send stearic acid and ammonia continuously and quantitatively into the liquid phase reaction tower for ammoniation at 350 ℃ to generate octadecane nitrile.
After washing with water and refinement, Octadecylamine was sent to the autoclave and was subject to hydrogenation reaction under 130 ℃ and the pressure of about 3.5MPa with the nickel catalyst for generation of Octadecanamine.
The hydrogenated product was subject to precipitation for removing the catalyst to derive the final products.
During laboratory preparation, the octadecane nitrile and anhydrous ethanol are subject to boiling under reflux and further put into sodium metal for reaction.
Pour the reaction mixture into the dilute hydrochloric acid with cooling obtaining the Octadecanamine hydrochloride.
Further treat with 20% sodium hydroxide solution treated with 20% sodium hydroxide solution can produce Octadecanamine. The yield is 85%.
Fixed consumption amount of material: stearic acid: 1165kg/t, ammonia 151kg/t, hydrogen gas: 211m3, nickel catalyst: 6kg/t.
Production Methods
Octadecylamine is manufactured under the trade names of Adogen 142D (Ashland), Alamine 7D (General Mills), Armeen 18D (Armak), Kemamine P- 990D (Humko), and Jetamine 18D (Jetco).
Reactivity Profile
Octadecylamine neutralizes acids in exothermic reactions to form salts plus water.
May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.
Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
